Chris Wiegman Chris Wiegman

A Developer Looks at 40

Tomorrow I hit a big milestone in my life. I turn 40. Normally birthdays aren’t something I think too much of but this one hit me a little bit harder than I expected. My life today is, I must admit, vastly different from where I thought I would be at this point when I hit 20 or even when I hit 30. It’s even so much different from what I thought it would be even 5 years ago and, for the most part, that’s all a very good thing.

Looking Back

Twenty years ago I thought I had my life all planned out. I was about to start back to school to learn to fly airplanes and I really thought I was starting on something that would last a lifetime. I was looking forward to, what I thought at the time, was going to be something exciting and fulfilling and it seemed like nothing was going to slow me down.

Ten years later, when I turned 30, things looked a lot different. Flying, it turned out, was actually about as exciting to me as watching the grass grow while in a tiny room with over one hundred angry people. I was bored to tears and, as a result, I had been building websites on the side for SIU that with the recession turned into an opportunity to get back to school for a career where I could actually build something. I was working on a degree in computer science and figured I would, if I was lucky, get to build sites for SIU or another university for a long time to come. 

Really, at 30 I pretty much had it all. I was no longer a glorified bus driver, I was making a little more money and I got to wake up every morning knowing what city I was in without having to look forward to dealing with yet another airport. Life was pretty good.

Frankly, all of my thirties were pretty damn good. I finished a master’s degree, moved to Austin, built and sold a small company, moved to the beach, spoke 50 times all over the world including my last talk which was a keynote for a tech conference, designed and taught my own university course and generally enjoyed my time at home with Joy and traveling all over with a chance, this time around, to actually get to enjoy the places I travelled to. What more could I ask for?


Today Joy and I are happily living in Florida, working from home and traveling the world on our own schedule. After three years of relative quiet while we settled in I’m starting new projects, speaking to bigger audiences and working for one of the biggest and best universities in the country where I was sought at for my experience with WordPress and web development in general.

I’m also restless.

I haven’t touched an airplane in 10 years and, while I hated the idea of an airline and flying jets around in general, I actually do miss teaching it. While it wasn’t a lucrative career flight instructing was incredibly rewarding and, even after promising myself numerous times I would get back to it, I still haven’t had a chance to move on it.

I’m near my heaviest weight of all time as well. Working from home really is wonderful but it sure makes it hard to get enough exercise. I say “near my heaviest” as, three months ago, I joined a new gym, found a personal trainer I like and have started to get myself back in shape but I’ve got a long way to go on that one. It turns out the downside to being happy and comfortable is it comes with a lot of snacks and getting out of the house isn’t always the easiest thing during the work day. Our drinking has helped with this either. It turns out that living in your dream neighborhood, where you can walk everywhere including dozens of bars, makes going to the bar the easiest thing in the world after a long day. It’s a trap Joy and I have both fallen into and we need to step up our efforts to get out of.

With both of these I’ve even contemplated going back to the airlines as I feel like, compared to what I’m doing now, it would be fairly easy and, honestly, there are days when a break from the daily challenges of my work would be nice. That said, it only takes a few minutes of those thoughts to remember how bored I was last time and realize that isn’t the answer.

I also haven’t built any major projects on my own in over three years. The biggest project I had, which served me well at work and elsewhere, turned out to suck pretty much all the time I had for any other side work.

All in all, life is pretty good right now, restless or otherwise. I still drink to much, I need to lose more weight and I want to find an exciting project while getting back to teaching people to fly but… We all need goals, right? In the big scheme of things I think those are probably good problems to have.

Looking Ahead

So what is the point going forward? The truth is, for the first time at a major birthday for me, I don’t really know what the future brings. Looking back professionally I realize I pretty much missed my 20s and find myself, today, where I probably should have been at 30 but that isn’t necessarily a bad thing.

This isn’t to say I don’t have goals for my 40’s. Joy and I both want to travel more. We want to walk the Camino de Santiago. I want to read and write more and get my fitness level back to a point where I’m not embarrassed to where most of my clothes. Those are all good goals, right?

Mostly, as I hit this new milestone, I look forward to not having to reinvent myself professionally over the next decade. I want to put my energy into building things that will help me and those around me while learning as much I can about the world around me, both are things I feel like I’ve put aside for far too long while trying to “make it” as either a pilot of a developer.

So as I look today at a new decade I do so without the aid of a crystal ball and with an ambition to live life rather than find it and I am quite alright with that outlook.